Condensed-cyclic compound and organic light emitting diode including organic layer containing the condensed-cyclic compound

ABSTRACT

A condensed-cyclic compound represented by Formula 1 below and an organic light emitting diode including the condensed-cyclic compound:

CROSS-REFERENCE TO RELATED APPLICATIONS

This application claims the benefit of Korean Patent Application No.10-2009-0096393, filed on Oct. 9, 2009, in the Korean IntellectualProperty Office, the disclosure of which is incorporated herein in itsentirety by reference.

BACKGROUND

1. Field

A condensed-cyclic compound, and an organic light emitting diodeincluding an organic layer containing the condensed-cyclic compound areprovided.

2. Description of the Related Technology

Organic light-emitting diodes (OLEDs), which are self-emitting devices,have advantages such as a wide viewing angle, excellent contrast, quickresponse, high brightness, excellent driving voltage characteristics,and can provide multicolored images.

A typical OLED has a structure including a substrate, and an anode, ahole transport layer (HTL), an emissive layer (EML), an electrontransport layer (ETL), and a cathode which are sequentially stacked onthe substrate in the order stated. In this regard, the HTL, the EML, andthe ETL are organic thin films formed of organic compounds.

An operating principle of an OLED having the above-described structureis as follows.

When a voltage is applied to the anode and the cathode, holes injectedfrom the anode move to the EML via the HTL, and electrons injected fromthe cathode move to the EML via the ETL. The holes and electronsrecombine in the EML to generate excitons. When the excitons drop froman excited state to a ground state, light is emitted.

SUMMARY OF CERTAIN INVENTIVE ASPECTS

A compound for providing an organic light emitting diode having highefficiency and long durability is provided.

According to an aspect of the present embodiments, there is provided acondensed-cyclic compound represented by Formula 1 below:

where R₈ and R₇ are each independently selected from the groupconsisting of a hydrogen atom, a halogen atom, a hydroxyl group, a cyanogroup, a substituted or unsubstituted C₁-C₃₀ alkyl group, a substitutedor unsubstituted C₂-C₃₀ alkenyl group, a substituted or unsubstitutedC₂-C₃₀ alkynyl group, a substituted or unsubstituted C₁-C₃₀ alkoxygroup, a group represented by —(Ar₁)_(a)—Ar₁₁, and a group representedby —N[—(Ar₂)_(b)—Ar₁₂][—(Ar₃)_(c)—Ar₁₃]; or R₈ is connected to * ofFormula 2 represented by

and R₇ is connected to *′ of Formula 2; R₁ through R₆, R₁₁ through R₁₄,and R₂₁ through R₂₄ are each independently selected from the groupconsisting of a hydrogen atom, a halogen atom, a hydroxyl group, a cyanogroup, a substituted or unsubstituted C₁-C₃₀ alkyl group, a substitutedor unsubstituted C₂-C₃₀ alkenyl group, a substituted or unsubstitutedC₂-C₃₀ alkynyl group, a substituted or unsubstituted C₁-C₃₀ alkoxygroup, a group represented by —(Ar₄)_(d)—Ar₁₄, and a group representedby —N[—(Ar₅)_(e)—Ar₁₅][—(Ar₆)_(f)—Ar₁₆]; Ar₁ through Ar₆ are eachindependently selected from the group consisting of a substituted orunsubstituted C₁-C₃₀ alkylene group, a substituted or unsubstitutedC₂-C₃₀ alkenylene group, a substituted or unsubstituted C₅-C₃₀ arylenegroup, and a substituted or unsubstituted C₄-C₃₀ heteroarylene group;Ar₁₁ through Ar₁₆ are each independently selected from the groupconsisting of a hydrogen atom, a halogen atom, a hydroxyl group, a cyanogroup, a substituted or unsubstituted C₁-C₃₀ alkyl group, a substitutedor unsubstituted C₂-C₃₀ alkenyl group, a substituted or unsubstitutedC₂-C₃₀ alkynyl group, a substituted or unsubstituted C₁-C₃₀ alkoxygroup, a substituted or unsubstituted C₅-C₃₀ aryl group, and asubstituted or unsubstituted C₄-C₃₀ heteroaryl group; a through f areeach independently an integer from 0 to 10; a Ar₁s in the grouprepresented by —(Ar₁)_(a)—Ar₁₁ are identical to or different from eachother, b Ar₂s in the group represented by —(Ar₂)_(b)—Ar₁₂ are identicalto or different from each other, c Ar₃s in the group represented by—(Ar₃)_(c)—Ar₁₃ are identical to or different from each other, d Ar₄s inthe group represented by —(Ar₄)_(d)—Ar₁₄ are identical to or differentfrom each other, e Ar₅s in the group represented by —(Ar₅)_(e)—Ar₁₅ areidentical to or different from each other, and f Ar₆s in the grouprepresented by [—(Ar₆)_(f)—Ar₁₆] are identical to or different from eachother; X₁ and X₂ are each independently a divalent linking groupselected from the group consisting of —C(Q₁)(Q₂)- and —N(Q₃)-; and Q₁through Q₃ are each independently selected from the group consisting ofa hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, asubstituted or unsubstituted C₁-C₃₀ alkyl group, a substituted orunsubstituted C₂-C₃₀ alkenyl group, a substituted or unsubstitutedC₂-C₃₀ alkynyl group, a substituted or unsubstituted C₁-C₃₀ alkoxygroup, a substituted or unsubstituted C₅-C₃₀ aryl group, and asubstituted or unsubstituted C₄-C₃₀ heteroaryl group.

R₁ through R₃ and R₄ through R₇ may be hydrogen; R₈ may be selected fromthe group consisting of hydrogen, a substituted or unsubstituted C₁-C₁₀alkyl group, a substituted or unsubstituted C₂-C₁₀ alkenyl group, asubstituted or unsubstituted C₂-C₁₀ alkynyl group, a substituted orunsubstituted C₁-C₁₀ alkoxy group, a group represented by—(Ar₁)_(a)—Ar₁₁, and a group represented by—N[—(Ar₂)_(b)—Ar₁₂][—(Ar₃)_(c)—Ar₁₃]; R₁₁ through R₁₄ may be eachindependently selected from the group consisting of hydrogen, asubstituted or unsubstituted C₁-C₁₀ alkyl group, a substituted orunsubstituted C₂-C₁₀ alkenyl group, a substituted or unsubstitutedC₂-C₁₀ alkynyl group, a substituted or unsubstituted C₁-C₁₀ alkoxygroup, a group represented by —(Ar₄)_(d)—Ar₁₄, and a group representedby —N[—(Ar₅)_(e)—Ar₁₅][—(Ar₆)_(f)—Ar₁₆]; Ar₁ through Ar₆ may be eachindependently selected from the group consisting of a substituted orunsubstituted C₁-C₃₀ alkylene group, a substituted or unsubstitutedC₂-C₃₀ alkenylene group, a substituted or unsubstituted C₅-C₃₀ arylenegroup, and a substituted or unsubstituted C₄-C₃₀ heteroarylene group;and Ar₁₁ and Ar₁₆ may be each independently selected from the groupconsisting of a hydrogen atom, a halogen atom, a hydroxyl group, a cyanogroup, a substituted or unsubstituted C₁-C₃₀ alkyl group, a substitutedor unsubstituted C₂-C₃₀ alkenyl group, a substituted or unsubstitutedC₂-C₃₀ alkynyl group, a substituted or unsubstituted C₁-C₃₀ alkoxygroup, a substituted or unsubstituted C₅-C₃₀ aryl group, and asubstituted or unsubstituted C₄-C₃₀ heteroaryl group.

BRIEF DESCRIPTION OF THE DRAWING

The above and other features and advantages of the present embodimentswill become more apparent by describing in detail exemplary embodimentsthereof with reference to the attached drawing in which:

FIG. 1 is a diagram schematically illustrating a structure of an organiclight emitting diode (OLED) according to an embodiment.

DETAILED DESCRIPTION OF CERTAIN INVENTIVE EMBODIMENTS

Hereinafter, the present embodiments will be described more fully withreference to the accompanying drawings, in which exemplary embodimentsare shown.

A condensed-cyclic compound represented by Formula 1 below is provided:

In Formula 1, R₈ and R₇ may be each independently selected from thegroup consisting of a hydrogen atom, a halogen atom, a hydroxyl group, acyano group, a substituted or unsubstituted C₁-C₃₀ alkyl group, asubstituted or unsubstituted C₂-C₃₀ alkenyl group, a substituted orunsubstituted C₂-C₃₀ alkynyl group, a substituted or unsubstitutedC₁-C₃₀ alkoxy group, a group represented by —(Ar₁)_(a)—Ar₁₁, and a grouprepresented by —N[—(Ar₂)_(b)—Ar₁₂][—(Ar₃)_(c)—Ar₁₃]; or R₈ may beconnected to * of Formula 2 represented by

and R₇ may be connected to *′ of Formula 2; and R₁ through R₆, R₁₁through R₁₄, and R₂₁ through R₂₄ may be each independently selected fromthe group consisting of a hydrogen atom, a halogen atom, a hydroxylgroup, a cyano group, a substituted or unsubstituted C₁-C₃₀ alkyl group,a substituted or unsubstituted C₂-C₃₀ alkenyl group, a substituted orunsubstituted C₂-C₃₀ alkynyl group, a substituted or unsubstitutedC₁-C₃₀ alkoxy group, a group represented by —(Ar₄)_(d)—Ar₁₄, and a grouprepresented by —N[—(Ar₅)_(e)—Ar₁₅][—(Ar₆)_(f)—Ar₁₆].

For example, in Formula 1, R₅ and R₇ may be each independently selectedfrom the group consisting of a hydrogen atom, a halogen atom, a hydroxylgroup, a cyano group, a substituted or unsubstituted C₁-C₃₀ alkyl group,a substituted or unsubstituted C₂-C₃₀ alkenyl group, a substituted orunsubstituted C₂-C₃₀ alkynyl group, a substituted or unsubstitutedC₁-C₃₀ alkoxy group, a group represented by —(Ar₁)_(a)—Ar₁₁, and a grouprepresented by —N[—(Ar₂)_(b)—Ar₁₂][—(Ar₃)_(c)—Ar₁₃], and R₁ through R₆and R₁₁ through R₁₄ may be each independently selected from the groupconsisting of a hydrogen atom, a halogen atom, a hydroxyl group, a cyanogroup, a substituted or unsubstituted C₁-C₃₀ alkyl group, a substitutedor unsubstituted C₂-C₃₀ alkenyl group, a substituted or unsubstitutedC₂-C₃₀ alkynyl group, a substituted or unsubstituted C₁-C₃₀ alkoxygroup, a group represented by —(Ar₄)_(d)—Ar₁₄, and a group representedby —N[—(Ar₅)_(e)—Ar₁₅][—(Ar₆)_(f)—Ar₁₆].

For example, in Formula 1, R₁ through R₃ and R₄ through R₇ may behydrogen; R₈ may be selected from the group consisting of hydrogen, asubstituted or unsubstituted C₁-C₁₀ alkyl group, a substituted orunsubstituted C₂-C₁₀ alkenyl group, a substituted or unsubstitutedC₂-C₁₀ alkynyl group, a substituted or unsubstituted C₁-C₁₀ alkoxygroup, a group represented by —(Ar₁)_(a)—Ar₁₁, and a group representedby —N[—(Ar₂)_(b)—Ar₁₂][—(Ar₃)_(c)—Ar₁₃]; R₁₁ through R₁₄ may be eachindependently selected from the group consisting of hydrogen, asubstituted or unsubstituted C₁-C₁₀ alkyl group, a substituted orunsubstituted C₂-C₁₀ alkenyl group, a substituted or unsubstitutedC₂-C₁₀ alkynyl group, a substituted or unsubstituted C₁-C₁₀ alkoxygroup, a group represented by —(Ar₄)_(d)—Ar₁₄, and a group representedby —N[—(Ar₅)_(e)—Ar₁₅][—(Ar₆)_(f)—Ar₁₆].

Ar₁ through Ar₆ may be each independently selected from the groupconsisting of a substituted or unsubstituted C₁-C₃₀ alkylene group, asubstituted or unsubstituted C₂-C₃₀ alkenylene group, an unsubstitutedC₅-C₃₀ arylene group, and a substituted or unsubstituted C₄-C₃₀heteroarylene group.

For example, Ar₁ through Ar₆ may be each independently selected from thegroup consisting of a substituted or unsubstituted C₁-C₁₀ alkylenegroup, a substituted or unsubstituted C₂-C₁₀ alkenylene group, asubstituted or unsubstituted C₅-C₁₄ arylene group, and a substituted orunsubstituted C₄-C₁₄ heteroarylene group.

Ar₁ through Ar₆ may be each independently selected from the groupconsisting of a substituted or unsubstituted ethylene group, asubstituted or unsubstituted phenylene group, a substituted orunsubstituted pentalenylene group, a substituted or unsubstitutedindenylene group, a substituted or unsubstituted naphthylene group, asubstituted or unsubstituted azulenylene group, a substituted orunsubstituted heptalenylene group, a substituted or unsubstitutedindacenylene group, a substituted or unsubstituted acenaphthylene group,a substituted or unsubstituted fluorenylene group, a substituted orunsubstituted phenalenylene group, a substituted or unsubstitutedphenanthrenylene group, a substituted or unsubstituted anthracenylenegroup, a substituted or unsubstituted fluoranthenylene group, asubstituted or unsubstituted triphenylenylene group, a substituted orunsubstituted pyrenylenylene group, a substituted or unsubstitutedchrysenylene group, a substituted or unsubstituted naphthacenylenegroup, a substituted or unsubstituted phenylene group, a substituted orunsubstituted perylenylene group, a substituted or unsubstitutedpentaphenylene group, a substituted or unsubstituted hexacenylene group,a substituted or unsubstituted pyrrolylene group, a substituted orunsubstituted pyrazolylene group, a substituted or unsubstitutedimidazolylene group, a substituted or unsubstituted imidazolinylenegroup, a substituted or unsubstituted imidazopyridinylene group, asubstituted or unsubstituted imidazopyrimidinylene group, a substitutedor unsubstituted pyridinylene group, a substituted or unsubstitutedpyrazinylene group, a substituted or unsubstituted pyrimidinylene group,a substituted or unsubstituted indolylene group, a substituted orunsubstituted purinylene group, a substituted or unsubstitutedquinolinylene group, a substituted or unsubstituted phthalazinylenegroup, a substituted or unsubstituted indolizinylene group, asubstituted or unsubstituted naphthyridinylene group, a substituted orunsubstituted quinazolinylene group, a substituted or unsubstitutedcinnolinylene group, a substituted or unsubstituted indazolylene group,a substituted or unsubstituted carbazolylene group, a substituted orunsubstituted phenazinylene group, a substituted or unsubstitutedphenanthridinylene group, a substituted or unsubstituted pyranylenegroup, a substituted or unsubstituted chromenylene group, a substitutedor unsubstituted benzofuranylene group, a substituted or unsubstitutedthiophenylene group, a substituted or unsubstituted benzothiophenylenegroup, a substituted or unsubstituted isothiazolylene group, asubstituted or unsubstituted benzimidazolylene group, and a substitutedor unsubstituted isoxazolylene group, but are not limited thereto.

Ar₁₁ through Ar₁₆ may be each independently selected from the groupconsisting of a hydrogen atom, a halogen atom, a hydroxyl group, a cyanogroup, a substituted or unsubstituted C₁-C₃₀ alkyl group, a substitutedor unsubstituted C₂-C₃₀ alkenyl group, a substituted or unsubstitutedC₂-C₃₀ alkynyl group, a substituted or unsubstituted C₁-C₃₀ alkoxygroup, a substituted or unsubstituted C₅-C₃₀ aryl group, and asubstituted or unsubstituted C₄-C₃₀ heteroaryl group.

Ar₁₁ through Ar₁₆ may be each independently selected from the groupconsisting of a substituted or unsubstituted C₁-C₁₀ alkyl group, asubstituted or unsubstituted C₁-C₁₀ alkoxy group, a substituted orunsubstituted phenyl group, a substituted or unsubstituted pentalenylgroup, a substituted or unsubstituted indenyl group, a substituted orunsubstituted naphthyl group, a substituted or unsubstituted azulenylgroup, a substituted or unsubstituted heptalenyl group, a substituted orunsubstituted indacenyl group, a substituted or unsubstitutedacenaphthyl group, a substituted or unsubstituted fluorenyl group, asubstituted or unsubstituted phenalenyl group, a substituted orunsubstituted phenantlenyl group, a substituted or unsubstitutedanthracenyl group, a substituted or unsubstituted fluoranthenyl group, asubstituted or unsubstituted triphenylenyl group, a substituted orunsubstituted pyrenyl group, a substituted or unsubstituted chrysenylgroup, a substituted or unsubstituted naphthacenyl group, a substitutedor unsubstituted picenyl group, a substituted or unsubstituted perylenylgroup, a substituted or unsubstituted pentacenyl group, a substituted orunsubstituted hexacenyl group, a substituted or unsubstituted pyrrolylgroup, a substituted or unsubstituted pyrazolyl group, a substituted orunsubstituted imidazolyl group, a substituted or unsubstitutedimidazolinyl group, a substituted or unsubstituted imidazopyridinylgroup, a substituted or unsubstituted imidazopyrimidinyl group, asubstituted or unsubstituted pyridinyl group, a substituted orunsubstituted pyrazinyl group, a substituted or unsubstitutedpyrimidinyl group, a substituted or unsubstituted indolyl group, asubstituted or unsubstituted furinyl group, a substituted orunsubstituted quinolinyl group, a substituted or unsubstitutedphthalazinyl group, a substituted or unsubstituted indolizinyl group, asubstituted or unsubstituted naphthyridinyl group, a substituted orunsubstituted quinazolinyl group, a substituted or unsubstitutedcinolinyl group, a substituted or unsubstituted indazolyl group, asubstituted or unsubstituted carbazolyl group, a substituted orunsubstituted phenazinyl group, a substituted or unsubstitutedphenanthridinyl group, a substituted or unsubstituted pyranylene group,a substituted or unsubstituted chromenyl group, a substituted orunsubstituted benzofuranyl group, a substituted or unsubstitutedthiophenyl group, a substituted or unsubstituted benzothiophenyl group,a substituted or unsubstituted isothiazolyl group, a substituted orunsubstituted benzimidazolyl group, and a substituted or unsubstitutedisoxazolyl group, but are not limited thereto.

For example, Ar₁ through Ar₆ may be each independently selected from thegroup consisting of a pyridinylene group, a quinolinylene group, abenzimidazolylene group, an imidazopyridinylene group, animidazopyrimidinylene group, a phenylene group, a C₁-C₁₀ alkyl phenylenegroup, a carbazolylene group, a phenylcarbazolylene group, afluorenylene group, a C₁-C₁₀ alkyl fluorenylene group, a di(C₁-C₁₀alkyl)fluorenylene group, an ethylene group, and a naphthylene group,but are not limited thereto.

Also, for example, Ar₁₁ through Ar₁₆ may be each independently selectedfrom the group consisting of a methyl group, an ethyl group, a propylgroup, a butyl group, a methoxy group, an ethoxy group, a propoxy group,a butoxy group, a pyridinyl group, a quinolinyl group, a benzimidazolylgroup, an imidazopyridinyl group, an imidazopyrimidinyl group, a phenylgroup, a carbazolyl group, a fluorenyl group, a di(C₁-C₁₀alkyl)fluorenyl group, a naphthyl group, and a functional grouprepresented by the formula

but are not limited thereto.

R₈ and R₁₁ through R₁₄ may be each independently selected from the groupconsisting of functional groups represented by Formulae 3A through 3Obelow, but are not limited thereto:

In Formulae 3A through 3O, Z₁ and Z₂ are each independently selectedfrom the group consisting of hydrogen, a hydroxyl group, a methyl group,an ethyl group, a propyl group, a butyl group, a methoxy group, anethoxy group, a propoxy group, a butoxy group, a phenyl group, and anaphthyl group.

R₈ and R₁₁ through R₁₄ may be each independently selected from the groupconsisting of compounds represented by Formulae 4A through 4R below, butare not limited thereto:

In Formula 1, a through f may be each independently an integer from 0 to10. For example, a through f may be each independently 0, 1, or 2, butare not limited thereto.

In Formula 1, a Ar₁s in the group represented by —(Ar₁)_(a)—Ar₁₁ may beidentical to or different from each other, b Ar₂s in the grouprepresented by —(Ar₂)_(b)—Ar₁₂ may be identical to or different fromeach other, c Ar₃s in the group represented by —(Ar₃)_(c)—Ar₁₃ may beidentical to or different from each other, d Ar₄s in the grouprepresented by —(Ar₄)_(d)—Ar₁₄ may be identical to or different fromeach other, e Ar₅s in the group represented by —(Ar₅)_(e)—Ar₁₅ may beidentical to or different from each other, and f Ar₆s in the grouprepresented by [—(Ar₆)_(f)—Ar₁₆] may be identical to or different fromeach other.

For example, in the group represented by —(Ar₁)_(a)—Ar₁₁, when a is 2,the two Ar₁s may be both phenylene groups, or one of the two may be aphenylene group and the other may be a benzimidazolylene group.

In Formula 1, Q₁ through Q₃ may be each independently selected from thegroup consisting of hydrogen, a C₁-C₃₀ alkyl group, a C₁-C₃₀ alkoxygroup, a C₅-C₁₄ aryl group, and a C₄-C₁₄ heteroaryl group. For example,Q₁ through Q₃ may be each independently selected from the groupconsisting of hydrogen, a methyl group, an ethyl group, a propyl group,a butyl group, a methoxy group, an ethoxy group, a propoxy group, abutoxy group, a phenyl group, and a naphthyl group, but are not limitedthereto. For example, Q₁ through Q₃ may be each independently hydrogen,a methyl group, or a phenyl group.

In Formula 1, X₁ may be selected from the group consisting of —CH₂—,—CH(CH₃)—, —C(CH₃)₂—, —CH(Ph)-, —NH—, and —N(Ph)-, wherein Ph denotes aphenyl group, but is not limited thereto.

Accordingly, the condensed-cyclic compound of Formula 1 has high thermalstability. Also, since the condensed-cyclic compound has a wide bandgap, the condensed-cyclic compound may be used for various layers, suchas a hole transport layer (HTL), an emissive layer (EML), and/or anelectron transport layer (ETL), of an organic light emitting diode(OLED), according to substituents, such as R₈ and R₁₁ through R₁₄.

In Formula 1, R₈ may be connected to * of Formula 2 below and R₇ may beconnected to *′ of Formula 2.

Accordingly, the condensed-cyclic compound represented by Formula 1 maybe represented by Formula 1A below:

In Formula 1A, R₁ through R₆ and R₁₁ through R₁₄ are as described above,and R₂₁ through R₂₄ are as described in connection with R₁₁ through R₁₄.

For example, in Formula 1A, R₁ through R₆ may be hydrogen; R₁₁ throughR₁₄ and R₂₁ through R₂₄ may each independently hydrogen, a substitutedor unsubstituted C₁-C₁₀ alkyl group, a substituted or unsubstitutedC₂-C₁₀ alkenyl group, a substituted or unsubstituted C₂-C₁₀ alkynylgroup, a substituted or unsubstituted C₁-C₁₀ alkoxy group, a grouprepresented by —(Ar₄)_(d)—Ar₁₄, and a group represented by—N[—(Ar₅)_(e)—Ar₁₅][—(Ar₆)_(f)—Ar₁₆].

Here, Ar₄ through Ar₆, A₁₄ through Ar₁₆, and d through f are asdescribed above.

In Formula 1A, R₁₁ through R₁₄ and R₂₁ through R₂₄ may be eachindependently selected from the group consisting of the compoundsrepresented by Formulae 3A through 3O, but are not limited thereto.

In Formula 1A, R₁₁ through R₁₄ and R₂₁ through R₂₄ may be eachindependently selected from the group consisting of the functionalgroups represented by Formulae 4A through 4R, but are not limitedthereto.

In Formula 1A, Q₁ through Q₃ and X₁ are as described above, and X₂ is asdescribed above in connection with X₁.

Since the condensed-cyclic compound of Formula 1 may be represented byFormula 1A, the condensed-cyclic compound has high thermal stability.Also, since the condensed-cyclic compound has a wide band gap, thecondensed-cyclic compound may be used for various layers, such as a HTL,an EML, and/or an ETL, of an OLED, according to substituents, such as R₈and R₁₁ through R₁₄.

According to an embodiment, in Formula 1, R₁ through R₃ and R₄ throughR₇ may be hydrogen; R₈ and R₁₁ through R₁₄ may be each independentlyselected from the group consisting of hydrogen and functional groupsrepresented by Formulae 3A through 3O; and X₁ may be a divalent linkinggroup selected from the group consisting of —C(Q₁)(Q₂)- and —N(Q₃)-,wherein Q₁ through Q₃ may be each independently selected from the groupconsisting of hydrogen, a methyl group, an ethyl group, a propyl group,a butyl group, a methoxy group, an ethoxy group, a propoxy group, abutoxy group, a phenyl group, and a naphthyl group.

According to another embodiment, in Formula 1, R₁ through R₃, R₄ throughR₇, R₁₁, R₁₃, and R₁₄ may be hydrogen; R₈ and R₁₂ may be eachindependently selected from the group consisting of hydrogen and thefunctional groups represented by Formulae 3A through 3O; and X₁ may be adivalent linking group selected from the group consisting of —C(Q₁)(Q₂)-and —N(Q₃)-, wherein Q₁ through Q₃ may be each independently selectedfrom the group consisting of hydrogen, a methyl group, an ethyl group, apropyl group, a butyl group, a methoxy group, an ethoxy group, a propoxygroup, a butoxy group, a phenyl group, and a naphthyl group.

According to another embodiment, in Formula 1, R₁ through R₃, R₄ throughR₇, R₁₁, R₁₃, and R₁₄ may be hydrogen; R₈ and R₁₂ may be eachindependently selected from the group consisting of hydrogen and thefunctional groups represented by Formulae 4A through 4R; and X₁ may beselected from the group consisting of —CH₂—, —CH(CH₃)—, —C(CH₃)₂—,—CH(Ph)-, —NH—, and —N(Ph)-, wherein Ph denotes a phenyl group.

According to another embodiment, in Formula 1, R₁ through R₃, R₄ throughR₇, R₁₁, R₁₃, and R₁₄ may be hydrogen; R₈ and R₁₂ may be eachindependently selected from the group consisting of hydrogen and thefunctional groups represented by Formulae 4A through 4R; and X₁ may beselected from the group consisting of —CH₂—, —CH(CH₃)—, —C(CH₃)₂—, and—CH(Ph)-, wherein Ph denotes a phenyl group.

According to an embodiment, in Formula 1, R₈ may be connected to * ofFormula 2, R₇ may be connected to *′ of Formula 2 (that is, Formula 1 isrepresented by Formula 1A), R₁ through R₆ may be hydrogen; R₁₁ throughR₁₄ and R₂₁ through R₂₄ may be each independently selected from thegroup consisting of hydrogen and the functional groups represented byFormulae 3A through 3O; and X₁ and X₂ may be each independently adivalent linking group selected from the group consisting of —C(Q₁)(Q₂)-and —N(Q₃)-, wherein Q₁ through Q₃ may be each independently selectedform the group consisting of hydrogen, a methyl group, an ethyl group, apropyl group, a butyl group, a methoxy group, an ethoxy group, a propoxygroup, a butoxy group, a phenyl group, and a naphthyl group.

According to another embodiment, in Formula 1, R₈ may be connected to *of Formula 2, R₇ may be connected to *′ of Formula 2 (that is, Formula 1is represented by Formula 1A), R₁ through R₆, R₁₁, R₁₃, R₁₄, R₂₁, R₂₃,and R₂₄ may be hydrogen; R₁₂ and R₂₂ may be each independently selectedfrom the group consisting of hydrogen and the functional groupsrepresented by Formulae 3A through 3O; and X₁ and X₂ may be eachindependently a divalent linking group selected from the groupconsisting of —C(Q₁)(Q₂)- and —N(Q₃)-, wherein Q₁ through Q₃ may be eachindependently selected from the group consisting of hydrogen, a methylgroup, an ethyl group, a propyl group, a butyl group, a methoxy group,an ethoxy group, a propoxy group, a butoxy group, a phenyl group, and anaphthyl group.

According to another embodiment, in Formula 1, R₈ may be connected to *of Formula 2, R₇ may be connected to *′ of Formula 2 (that is, Formula 1is represented by Formula 1A); R₁ through R₆, R₁₁, R₁₃, R₁₄, R₂₁, R₂₃,and R₂₄ may be hydrogen; R₁₂ and R₂₂ may be each independently selectedfrom the group consisting of hydrogen and the functional groupsrepresented by Formulae 4A through 4R; and X₁ and X₂ may be eachindependently selected from the group consisting of —CH₂—, —CH(CH₃)—,—C(CH₃)₂—, —CH(Ph)-, —NH—, and —N(Ph)-, wherein Ph denotes a phenylgroup.

According to another embodiment, in Formula 1, R₈ may be connected to *of Formula 2, R₇ may be connected to *′ of Formula 2 (that is, Formula 1is represented by Formula 1A); R₁ through R₆, R₁₁, R₁₃, R₁₄, R₂₁, R₂₃,and R₂₄ are hydrogen; R₁₂ and R₂₂ may be each independently selectedfrom the group consisting of hydrogen and the functional groupsrepresented by Formulae 4A through 4R; and X₁ and X₂ may be eachindependently selected from the group consisting of —CH₂—, —CH(CH₃)—,—C(CH₃)₂—, and —CH(Ph)-.

According to another embodiment, the condensed-cyclic compoundrepresented by Formula 1 may be one of Compounds 1 to 43 below, but isnot limited thereto.

Examples of the unsubstituted C₁-C₃₀ alkyl group or the C₁-C₃₀ alkylgroup used herein include methyl, ethyl, propyl, isobutyl, sec-butyl,pentyl, iso-amyl, hexyl, and the like. In the substituted C₁-C₃₀ alkylgroup, at least one hydrogen atom of the unsubstituted C₁-C₃₀ alkylgroup may be substituted with a halogen atom, a hydroxyl group, a nitrogroup, a cyano group, an amino group, an amidino group, hydrazine,hydrazone, a carboxyl group or salts thereof, a sulfonic acid group orsalts thereof, a phosphoric acid or salts thereof, a C₁-C₃₀ alkyl group,a C₁-C₃₀ alkenyl group, a C₁-C₃₀ alkynyl group, a C₆-C₃₀ aryl group, ora C₂-C₂₀ heteroaryl group. The substituted or unsubstituted C₁-C₃₀alkylene group has the same structure as the substituted orunsubstituted C₁-C₃₀ alkyl group as described above, but is a divalentlinking group.

The unsubstituted C₁-C₃₀ alkoxy group or the C₁-C₃₀ alkoxy group may bea group represented by —OA, wherein A is the unsubstituted C₁-C₃₀ alkylgroup, and examples of the unsubstituted C₁-C₃₀ alkoxy group aremethoxy, ethoxy, and isopropyloxy. At least one hydrogen atom in theunsubstituted C₁-C₃₀ alkoxy group may be substituted with thesubstituents described with reference to the substituted C₁-C₃₀ alkylgroup.

The unsubstituted C₂-C₃₀ alkenyl group or the C₂-C₃₀ alkenyl group hasat least one carbon-carbon double bond in the center or at one end ofthe unsubstituted C₂-C₃₀ alkyl group structure. Examples of theunsubstituted alkenyl group include ethenyl, propenyl, and butenyl. Atleast one hydrogen atom in the unsubstituted C₂-C₃₀ alkenyl group may besubstituted with the substituents described with reference to thesubstituted C₁-C₃₀ alkyl group. The substituted or unsubstituted C₂-C₃₀alkenylene group has the same structure as the substituted orunsubstituted C₂-C₃₀ alkenyl group described above, but is a divalentlinking group.

The unsubstituted C₂-C₃₀ alkynyl group or the C₂-C₃₀ alkynyl group has acarbon-carbon triple bond in the center or at one end of the C₂-C₃₀alkyl group structure. Examples of the unsubstituted C₂-C₃₀ alkynylgroup and acetylene, propylene, isopropylacetylene, andt-butylacetylene. At least one hydrogen atom in the alkynyl group may besubstituted with the substituents described with reference to thesubstituted C₁-C₃₀ alkyl group.

The unsubstituted C₅-C₃₀ aryl group is a monovalent group having acarbocyclic aromatic system having 5 to 30 carbon atoms including atleast one aromatic ring. The unsubstituted C₅-C₃₀ arylene group is adivalent group having a carbocyclic aromatic system having 5 to 30carbon atoms including at least one aromatic ring. When the aryl groupand the arylene group have at least two rings, the at least two ringsmay be fused to each other. At least one hydrogen atom in the aryl groupand the arylene group may be substituted with the substituents describedwith reference to the substituted C₁-C₃₀ alkyl group.

Examples of the substituted or unsubstituted C₅-C₃₀ aryl group are aphenyl group, a C₁-C₁₀ alkylphenyl group (e.g., an ethylphenyl group), aC₁-C₁₀ alkylbiphenyl group (e.g., an ethylbiphenyl group), a halophenylgroup (e.g., an o-, m- or p-fluorophenyl group and a dichlorophenylgroup), a dicyanophenyl group, a trifluoromethoxyphenyl group, an o-, m-or p-tolyl group, an o-, m- or p-cumenyl group, a mesityl group, aphenoxyphenyl group, a (α,α-dimethylbenzene)phenyl group, a(N,N′-dimethyl)aminophenyl group, a (N,N′-diphenyl)aminophenyl group, apentalenyl group, an indenyl group, a naphthyl group, a halonaphthylgroup (e.g., a fluoronaphthyl group), a C₁-C₁₀ alkylnaphthyl group(e.g., a methylnaphthyl group), a C₁-C₁₀ alkoxynaphthyl group (e.g., amethoxynaphthyl group), an anthracenyl group, an azulenyl group, aheptalenyl group, an acenaphthylenyl group, a phenalenyl group, afluorenyl group, an anthraquinolyl group, a methylanthryl group, aphenanthryl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, an ethyl-chrysenyl group, a picenyl group, a perylenyl group, achloroperylenyl group, a pentaphenyl group, a pentacenyl group, atetraphenylenyl group, a hexaphenyl group, hexacenyl group, a rubicenylgroup, a coronenyl group, a trinaphthylenyl group, a heptaphenyl group,a heptacenyl group, a pyranthrenyl group, and an ovalenyl group.Examples of the substituted or unsubstituted C₅-C₃₀ arylene group may beeasily derived from examples of the substituted or unsubstituted C₅-C₃₀aryl group.

The unsubstituted C₄-C₃₀ heteroaryl group is a monovalent group havingat least one aromatic ring having at least one of the hetero atomsselected from the group consisting of N, O, P, and S. The unsubstitutedC₂-C₃₀ heteroarylene group is a divalent group having at least onearomatic ring having at least one of the hetero atoms selected from thegroup consisting of N, O, P, and S. In this regard, when the heteroarylgroup and the heteroarylene group have at least two rings, the at leasttwo rings may be fused with each other. At least one hydrogen atom inthe heteroaryl group and the heteroarylene group may be substituted withthe substituents described with reference to the substituted C₁-C₃₀alkyl group.

Examples of the unsubstituted C₄-C₃₀ heteroaryl group include apyrazolyl group, an imidazolyl group, an oxazolyl group, a thiazolylgroup, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, apyridinyl group, a pyridazinyl group, a pyrimidinyl group, a triazinylgroup, a carbazolyl group, an indolyl group, a quinolinyl group, anisoquinolinyl group, a benzimidazolyl group, an imidazopyridinyl groupand an imidazopyrimidinyl group. Examples of the substituted andunsubstituted C₄-C₃₀ heteroarylene group may be easily derived fromexamples of the substituted or unsubstituted C₄-C₃₀ arylene group.

The condensed-cyclic compound of Formula 1 may be synthesized using anorganic synthesis method. A method of synthesizing the condensed-cycliccompound may be referred to embodiments that will be described later.

For example, Reaction Scheme 1A below is a reaction scheme forsynthesizing the condensed-cyclic compound of Formula 1:

In Reaction Scheme 1A, R1 through R8, R11 through R14, and X1 aredefined as described above.

In Reaction Scheme 1A, Ha denotes a halogen atom, and may be —F, —Cl,—Br, or —I.

In Reaction Scheme 1A, A1 may be a hydrogen atom,

or —B(OH)2, but is not limited thereto and may be selected from wellknown various moiety according to selected R8.

Reaction Scheme 1A is an example of a method of synthesizing thecondensed-cyclic compound of Formula 1, and one of ordinary skill in theart may synthesize the condensed-cyclic compound of Formula 1 by using awell-known organic synthesis method by referring to Reaction Scheme 1Aand the structure of the compound of Formula 1.

The condensed-cyclic compound of Formula 1 may be used in an organiclayer of an OLED. An embodiment provides an OLED including a firstelectrode, a second electrode, and an organic layer disposed between thefirst electrode and the second electrode, wherein the organic layerincludes the condensed-cyclic compound of Formula 1 described above.

Here, the organic layer may be an EML, a HTL, or an ETL, but is notlimited thereto. When the condensed-cyclic compound of Formula 1 is usedas an EML, the condensed-cyclic compound may be used as a host or adopant.

FIG. 1 is a diagram schematically illustrating a structure of an OLED 10according to an embodiment. Hereinafter, a structure of the OLED 10 anda method of manufacturing the OLED 10 according to an embodiment willnow be described with reference to FIG. 1.

The OLED 10 includes a substrate 11, a first electrode 13, an organiclayer 15, and a second electrode 17, which are sequentially stacked inthis order.

The substrate 11, which may be any substrate that is used inconventional OLEDs, may be a glass substrate or a transparent plasticsubstrate with excellent mechanical strength, thermal stability,transparency, surface smoothness, ease of handling, and waterproofness.

The first electrode 13 may be formed by depositing or sputtering amaterial that is used to form the first electrode 13 on the substrate.When the first electrode 13 constitutes an anode, the material used toform the first electrode 13 may be a high work-function material so asto facilitate hole injection. The first electrode 13 may be a reflectiveelectrode or a transparent electrode. Transparent and conductivematerials such as indium tin oxide (ITO), indium zinc oxide (IZO), tindioxide (SnO2), and zinc oxide (ZnO) may be used to form the firstelectrode 13. Alternatively, the first electrode 13 may be formed byusing magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium(Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or the like.

The organic layer 15 may be disposed on the first electrode 13. The term“organic layer” used herein indicates any layer interposed between thefirst electrode 13 and the second electrode 17. The organic layer 15 maynot be formed of pure organic materials, and may also include a metalcomplex.

The organic layer 15 may include at least one of a hole injection layer(HIL), a HTL, an EML, a hole blocking layer (HBL), an ETL and anelectron injection layer (EIL).

The HIL may be formed on the first electrode 13 by using a vacuumdeposition method, a spin coating method, a casting method, aLangmuir-Blodgett (LB) method, or the like.

When the HIL is formed by using a vacuum deposition method, vacuumdeposition conditions may vary according to a compound that is used toform the HIL, and the desired structure and thermal properties of theHIL to be formed. In general, however, the vacuum deposition method maybe performed at a deposition temperature of about 100° C. to about 500°C., under a pressure of about 10-8 torr to about 10-3 torr, and at adeposition rate of about 0.01 to about 100 Å/sec.

When the HIL is formed by using a spin coating method, the coatingconditions may vary according to a compound that is used to form theHIL, and the desired structure and thermal properties of the HIL to beformed. In general, however, conditions for the spin coating method mayinclude a coating rate of about 2,000 rpm to about 5,000 rpm and a heattreatment temperature of about 80° C. to about 200° C., wherein the heattreatment is performed to remove a solvent after coating.

The HIL may be formed of any well known hole injecting material.Examples of the hole injecting material includeN,N′-diphenyl-N,N′-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4′-diamine(DNTPD), a phthalocyanine compound such as copperphthalocyanine,4,4′,4″-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), TDATA,2T-NATA, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonicacid (Pani/CSA), and(polyaniline)/poly(4-styrenesulfonate) (PANI/PSS), but are not limitedthereto.

The thickness of the HIL may be about 100 Å to about 10000 Å, and forexample, about 100 Å to about 1000 Å. When the thickness of the HIL iswithin this range, the HIL may have excellent hole injecting abilitywithout a substantial increase in driving voltage.

Then, the HTL may be formed on the HIL by using a vacuum depositionmethod, a spin coating method, a casting method, a LB method, or thelike. When the HTL is formed by using a vacuum deposition method or aspin coating method, the conditions for deposition and coating may besimilar to those for the formation of the HIL, although the conditionsfor the deposition and coating may vary according to the material thatis used to form the HTL.

A HTL material may include the condensed-cyclic compound of Formula 1described above. Alternatively, the HTL may be formed of any materialthat is commonly used to form a HTL. Examples of the material that isused to form the HTL include: a carbazole derivative such asN-phenylcarbazole and polyvinylcarbazole; an amine derivative having anaromatic condensation ring such asN,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine(TPD), and N,N′-di(naphthalene-1-yl)-N,N′-diphenyl benzydine (α-NPD);and a triphenylamine-based material such as4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA). Among these materials,TCTA may not only transport holes but also inhibit excitons from beingdiffused into the EML.

The thickness of the HTL may be about 50 Å to about 1000 Å, and forexample, about 100 Å to about 800 Å. When the thickness of the HTL iswithin the range described above, the HTL may have excellent holetransporting ability without a substantial increase in driving voltage.

Then, an EML may be formed on the HTL by using a vacuum depositionmethod, a spin coating method, a casting method, an LB method, or thelike. When the EML is formed using a vacuum deposition method or a spincoating method, the conditions for deposition and coating may be similarto those for the formation of the HIL, although the conditions fordeposition and coating may vary according to the material that is usedto form the EML.

The EML may include the condensed-cyclic compound represented by Formula1 as previously described. The EML may include only the condensed-cycliccompound of Formula 1; include the condensed-cyclic compound of Formula1 as a host and a well known dopant; or include a well known host andthe condensed-cyclic compound of Formula 1 as a dopant. Examples of thewell known host include Alq₃, 4,4′-N,N′-dicarbazole-biphenyl (CBP),poly(n-vinylcarbazole) (PVK), 9,10-di(naphthalene-2-yl)anthracene (ADN),TCTA, 1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBI),3-tert-butyl-9,10-di-2-naphthylanthracene (TBADN), E3, anddistyrylarylene (DSA), but are not limited thereto.

Examples of a well known red dopant include PtOEP, Ir(piq)₃, andBtp₂Ir(acac), but are not limited thereto.

Also, examples of well known green dopant include Ir(ppy)₃(ppy=phenylpyridine), Ir(ppy)₂(acac), and Ir(mpyp)₃, but are not limitedthereto.

Examples of well known blue dopant include F₂Irpic, (F₂ppy)₂Ir(tmd),Ir(dfppz)₃, ter-fluorene, 4,4′-bis(4-diphenylaminostyryl)biphenyl(DPAVBi), and 2,5,8,11-tetra-t-butyl pherylene (TBP), but are notlimited to.

When the EML includes a host and a dopant, an amount of the dopant maybe generally in a range from about 0.01 to about 15 parts by weightbased on about 100 parts by weight of the host, but is not limitedthereto.

The thickness of the EML may be about 100 Å to about 1000 Å, and forexample, about 200 Å to about 600 Å. When the thickness of the EML iswithin this range, the EML may have excellent emitting ability without asubstantial increase in driving voltage.

When a phosphorescent dopant is also used to form the EML, a HBL may beformed between the HTL and the EML by using a vacuum deposition method,a spin coating method, a casting method, a LB method, or the like, inorder to prevent diffusion of triplet excitons or holes into an ETL.When the HBL is formed by using a vacuum deposition method or a spincoating method, the conditions for deposition and coating may be similarto those for the formation of the HIL, although the conditions fordeposition and coating may vary according to the material that is usedto form the HBL. Any material that is commonly used to form a HBL may beused. Examples of materials for forming the HBL include an oxadiazolederivative, a triazole derivative, and a phenanthroline derivative, butare not limited thereto.

The thickness of the HBL may be in the range of about 50 Å to about 1000Å, for example, about 100 Å to about 300 Å. When the thickness of theHBL is within these ranges, the HBL may have an excellent hole blockingability without a substantial increase in driving voltage.

Then, an ETL is formed by using a vacuum deposition method, a spincoating method, a casting method, or the like. When the ETL is formed byusing a vacuum deposition method or a spin coating method, thedeposition and coating conditions may be similar to those for formationof the HIL, although the deposition and coating conditions may varyaccording to a compound that is used to form the ETL. The ETL may beformed of the condensed-cyclic compound of Formula 1. Alternatively, amaterial that is used to form the ETL may be a material that stablytransports electrons injected from the electron injecting electrode(cathode) and any known material may be used. Examples of materials forforming the ETL include a quinoline derivative,tris(8-quinolinorate)aluminum (Alq₃), TAZ, Balq, and berylliumbis(benzoquinolin-10-olate) (bebq₂), but are not limited thereto.

The thickness of the ETL may be about 100 Å to about 1000 Å, and forexample, about 150 Å to about 500 Å. When the thickness of the ETL iswithin this range, the ETL may have satisfactory electron transportingability without a substantial increase in driving voltage.

Then, an EIL may be formed on the ETL. A material for forming the EIL isnot limited as long as it allows electrons to be easily injected fromthe cathode.

Examples of materials for forming the EIL include LiF, NaCl, CsF, Li₂O,and BaO, which are known in the art. Deposition conditions for formingthe EIL are similar to those for formation of the HIL, although thedeposition conditions may vary according to a material that is used toform the EIL.

The thickness of the EIL may be about 1 Å to about 100 Å, specificallyabout 3 Å to about 90 Å. When the thickness of the EIL is within thisrange, the EIL may have satisfactory electron injection ability withouta substantial increase in driving voltage.

Finally, the second electrode 17, which may be a transparent electrode,is disposed on the organic layer 15. The second electrode 17 may be acathode that is an electron injection electrode. Here, a secondelectrode forming metal may be a metal having a low work function, analloy having a low work function, an electro-conductive compound, ormixtures thereof. The second electrode 17 may be formed of lithium (Li),magnesium (Mg), aluminum (Al), aluminum (Al)-lithium (Li), calcium (Ca),magnesium (Mg)-indium (In), magnesium (Mg)-silver (Ag), or the like, andmay be formed as a thin film type transmission electrode. In addition,the transmission electrode may be formed of ITO or IZO to manufacture atop-emission type light-emitting device.

Hereinafter, one or more embodiments of the present embodiments will bedescribed in detail with reference to the following examples. However,these examples are not intended to limit the purpose and scope of theone or more embodiments.

EXAMPLES Synthesis Example 1 Synthesis of Compounds F and G

Compounds F and G were synthesized through Reaction Scheme 2 below:

Synthesis of Compound A

100 g (355.68 mmol) of 2-bromopyrene was mixed with 1 L oftetrahydrofuran (THF) in a flask, the temperature of the mixture in theflask was decreased to −78° C., 213.4 ml (533.52 mmol) of 2.5Mn-butyllithium (n-BuLi) in hexanes was slowly added dropwise to thedilution under a nitrogen atmosphere and then the resulting mixturethereof was stirred for 30 minutes. 99.41 mL (487.28 mmol) of2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was slowly to thereaction mixture, and then the flask was allowed to warm to roomtemperature.

The reaction was stopped by the addition of 1N (hydrochloric acid) HCl,and then were extracted with ethyl acetate (EA). Then, the extract waswashed with water and brine, dried over magnesium sulfate (MgSO₄), andconcentrated under reduced pressure. The concentrate was suspended inhexane and collected to give 75 g (yield=64%) of solid Compound A.

¹H-NMR (CDCl₃, 300 MHz) δ 1.48 (s, 12H), 7.97-8.04 (m, 3H), 8.07-8.22(m, 4H), 8.53 (d, J=6.9 Hz, 1H), 8.06 (d, J=9.3 Hz, 1H).

Synthesis of Compound B

85 g (258.98 mmol) of4,4,5,5-tetramethyl-2-(pyren-1-yl)-1,3,2-dioxaborolane, 45.23 mL (284.88mmol) of ethyl 2-bromobenzoate, 83.49 g (258.98 mmol) oftetrabutylammonium bromide, 259 mL (517.96 mmol) of 2M potassiumcarbonate, and 14.96 g (12.95 mmol) of Pd(PPh₃)₄ were combined intoluene. The resultant mixture was stirred while increasing thetemperature to ?, for 12 hours. The reaction was stopped by adding waterto the mixture, and was extracted with ethyl acetate. The organicextract was washed with water and brine, dried over MgSO₄, and thenconcentrated under reduced pressure. The concentrate was subjected tocolumn chromatography (ethyl acetate:Hexane (HEX)=1:50) so as to give 83g (yield=91.5%) of thin light yellow solid Compound B.

¹H-NMR (CDCl₃, 300 MHz) δ 0.38 (t, J=6.9 Hz, 3H), 3.66-3.81 (in, 2H),7.50 (d, J=6.9 Hz, 1H), 7.56-7.61, (m, 1H), 7.65-7.70 (m, 1H), 7.75 (d,J=9.3 Hz, 1H), 7.87 (d, J=7.8 Hz, 1H), 7.96-8.03 (m, 2H), 8.11 (m, 2H),8.13-8.14 (m, 2H), 8.20-8.22 (m, 2H).

Synthesis of Compound C

35 g (99.88 mmol) of Compound B was added to 500 mL of methanesulfonicacid, and the resultant reaction mixture was stirred at 75° C. for about4 hours. After checking that a starting material has disappeared by athin layer chromatography (TLC), the reaction mixture was cooled down to0° C. A red solid formed on cooling. The reaction mixture was stirredand the precipitate was collected by filtration. The filtrate was overwith MgSO₄ and concentrated under reduced pressure to give 29 g(yield=95%) of red solid Compound C.

¹H-NMR (300 MHz) δ 7.97-7.99 (m, 4H), 8.05-8.15 (m, 4H), 8.32 (m, 1H),8.44-8.49 (m, 2H) 8.75 (d, J=7.8 Hz, 1H), 9.36 (s, 1H).

Synthesis of Compound D

30 g (98.57 mmol) of Compound C was added to 500 mL of ethylene glycol,and followed by the addition of 148.08 mL (2957.1 mmol) of hydrazinehydrate. 132.74 g (2365.8 mmol) of potassium hydroxide was next added tothe reaction mixture, and the reaction mixture was stirred overnight ata temperature from 180° C. to 190° C. Next, the reaction mixture wascooled down to room temperature, and then poured into ice water. Aprecipitate was formed on neutralizing the reaction mixture by the slowaddition of 2N HCl. The precipitate was collected by filtration and wasdissolved in methylene chloride (MC) to give an organic layer. Theorganic layer was dried over MgSO₄, and then concentrated under reducedpressure. Accordingly, 10 g (yield=35%) of yellow solid Compound D wasobtained.

¹H-NMR (CDCl₃, 300 MHz) δ 4.29 (s, 2H), 7.41 (t, J=7.5 Hz, 1H), 7.55 (t,J=7.5 Hz, 1H), 7.72 (d, J=7.5 Hz, 1H), 8.00-8.09 (m, 3H), 8.20-8.27 (m,3H), 8.35 (s, 1H), 8.59 (d, J=7.5 Hz, 1H), 9.02 (d, J=6.3 Hz, 1H).

Synthesis of Compound E

55.1 mL (137.76 mmol) of 2.5M n-BuLi in hexanes was put into a flask at−78° C., and then 16 g (55.1 mmol) of Compound D that has been dissolvedin dried THF, was slowly added to the flask at −78° C. To the resultantreaction mixture was added 8.58 mL (137.76 mmol) of methyl iodide at−78° C., and the temperature was slowly increased to room temperature,and the reaction mixture was stirred for about 2 to 3 hours. Water waspoured to the reaction mixture and then the reaction mixture wasneutralized with 2N HCl. The reaction mixture were extracted withmelthylene chloride, dried over MgSO₄, concentrated under reducedpressure, and then purified with column chromatography (ethylacetate:hexane=1:100) to give obtain 11 g (yield=63%) of yellow solidCompound E.

¹H-NMR (CDCl₃, 300 MHz) δ 1.63 (s, 6H), 7.41 (t, J=7.2 Hz, 1H), 7.50 (t,J=7.2 Hz, 1H), 7.60 (d, J=7.5 Hz, 1H), 7.98 (t. J=7.2 Hz, 1H), 8.09-8.16(m, 2H), 8.19-8.26 (m, 4H), 8.53 (d, J=7.5 Hz, 1H), 9.00 (d, J=9.3 Hz,1H).

Synthesis of Compound F

11 g (34.55 mmol) of Compound E was dissolved in 80 mL of THF in a 1 Lround-bottom flask (RBF), and then 400 mL of methanol (MeOH) was slowlyadded to the RBF. 9.5 mL (76.00 mmol) of 48% hydrobromic acid was slowlyadded to the reactant in the resultant reaction mixture at 0° C.,followed by the slow addiction of 34.5% The temperature of the resultantreaction mixture was slowly increased from 0° C. to room temperature,while stirring the reaction mixture. After 2 the precipitate formed wasfiltered, dissolved in methylene chloride, washed with water,neutralized saturated NaHCO₃ solution, dried over MgSO₄, and thenconcentrated under reduced pressure. The concentrate was purified withcolumn chromatography to give 5.2 g (yield=31.6%) of yellow solidCompound F.

¹H-NMR (CDCl₃, 300 MHz) δ 1.70 (s, 6H), 7.45 (t, J=7.2 Hz, 1H) 7.52 (t,J=7.8 Hz, 1H), 7.63 (d, J=7.2 Hz, 1H), 8.21 (d, J=9.3 Hz, 1H), 8.32 (s,1H), 8.38 (d, J=9.3 Hz, 1H), 8.51-8.56 (m, 3H), 9.11 (d, J=9.9 Hz, 1H).

Synthesis of Compound G

7.8 g (yield=56%) of Compound G was obtained in the same manner as inSynthesis of Compound F, except that the reaction time was reduced to 8hours, instead of 2 days.

¹H-NMR (CDCl₃, 300 MHz) δ 1.70 (s, 6H), 7.24 (t, J=7.1 Hz, 1H) 7.45 (t,J=7.8 Hz, 1H), 7.52 (t, J=7.8 Hz, 1H), 7.61 (d, J=7.1 Hz, 1H), 8.21 (d,J=9.3 Hz, 1H), 8.32 (s, 1H), 8.38 (d, J=9.3 Hz, 1H), 8.51-8.56 (m, 3H),9.11 (d, J=9.9 Hz, 1H).

Synthesis Example 2 Synthesis of Compound 3

Compound 3 was synthesized through Reaction Scheme 3 below:

2.0 g (5.0 mmol) of Compound G and 1.84 g (5.5 mmol) of Compound H wereadded to a THF solution of 2.07 g (15.0 mmol) potassium carbonate, 173mg (3 mol %) of Pd(PPh₃)₄ was added to the resultant reaction mixturewith stirring, and the reaction mixture was heated for 24 hours. Themixture was cooled to room temperature extracted with dichloromethane.The organic layer was collected, dried over anhydrous magnesium sulfateand concentrated under reduced pressure. The concentrate was subjectedto a column chromatography (ethyl acetate:dichloromethane=3:7) to give2.07 g (yield=79%) of yellow solid Compound 3. The structure of Compound3 was identified using ¹H-NMR).

H NMR (CDCl₃, 300 MHz) δ 9.21 (1H), 8.82 (1H), 8.73 (1H), 8.18-8.03(4H), 7.81 (1H), 7.71-7.60 (8H), 7.45-7.43 (2H), 7.24 (2H), 1.71 (6H)

Synthesis Example 3 Synthesis of Compound 19

Compound 19 was synthesized through Reaction Scheme 4 below:

2.0 g (4.20 mmol) of Compound F and 2.58 g (12.6 mmol) of 3-pyridylboronacid pinacol ester were added to THF solution of 2.32 g (16.8 mmol)potassium carbonate, to this reaction mixture was added, 194 mg (4 mol%) of Pd(PPh₃)₄ was added with stirring, and the resultant reactionmixture was heated for 24 hours. The reaction mixture was cooled to roomtemperature and extracted with dichloromethane. Then, the organic layerwas collected, dried over anhydrous magnesium sulfate and concentratedunder reduced pressure. The concentrate was dried over columnchromatography (ethyl acetate:dichloromethane=3:7) to give 1.59 g(yield=80%) of yellow solid Compound 19. The structure of Compound 19was identified using ¹H-NMR.

H NMR (CDCl3, 300 MHz) δ 8.72 (2H), 8.51 (2H), 8.18-8.12 (2H), 8.02-7.97(3H), 7.85-7.81 (2H), 7.71-7.65 (5H), 7.45-7.41 (2H), 1.72 (6H)

Synthesis Example 4 Synthesis of Compound 40

Compound 40 was synthesized through Reaction Scheme 5 below:

Compound 40 was synthesized in the same manner as Synthesis Example 3,except that Compound G was used instead of Compound F, and phenylboronacid was used instead of 3-pyridylboron acid pinacol ester (yield=84%).The structure of Compound 40 was identified using ¹H-NMR.

H NMR (CDCl₃, 300 MHz) δ 8.21 (1H), 8.06-8.01 (2H), 7.81 (1H), 7.78-7.62(5H) 7.48-7.43 (3H), 7.32-7.25 (4H), 1.70 (6H)

Synthesis Example 5 Synthesis of Compound 35

Compound 35 was synthesized through Reaction Scheme 6 below:

2 g (5.0 mmol) of Compound G and 1.28 g (7.55 mmol) of diphenylamine wasdissolved in 50 mL of toluene. To this reaction mixture was added 2.40 g(25 mmol) of t-BuONa, 90.6 mg (2 mol %) oftris(dibenzylideneacetone)bispalladium (0) (Pd₂(dba)₃), and 20 mg (2 mol%) of (t-Bu)₃P were added thereto, and then the resultant reactionmixture was stirred for 4 hours at 90° C.

The reaction mixture was extracted 3 times by with 50 mL ofdichloromethane and the organic layers were combined. The combinedorganic layers were dried over magnesium sulfate then evaporated todryness. The residue was separately purified using silica gel columnchromatography to give 1.76 g (yield=72%) of Compound 35. The structureof Compound 35 was identified using ¹H-NMR.

¹H-NMR (300 MHz) δ 7.98 (1H) 7.87-7.81 (2H) 7.72-7.63 (5H), 7.44 (1H),7.21 (1H), 7.05-6.97 (6H), 6.65-6.46 (5H), 1.71 (6H)

Synthesis Example 6 Synthesis of Compound 34

Compound 34 was synthesized through Reaction Scheme 7 below:

2.4 g (5.0 mmol) of Compound F and 2.54 g (15.0 mmol) of diphenylaminewas dissolved in 100 mL of toluene. To this reaction mixture was added2.40 g (25 mmol) of t-BuONa, 137 mg (3 mol %) of Pd₂(dba)₃, and 30 mg (3mol %) of (t-Bu)3P and the resultant mixture was stirred for 6 hours at90° C.

The reaction mixture was extracted 3 times with 100 mL ofdichloromethane and the organic layers were combined. The combinedorganic layers were dried with magnesium sulfate then evaporated todryness. The residue was subjected to silica gel column chromatographyto give 2.27 g (yield=69%) of Compound 34. The structure of Compound 34was identified using 1H-NMR.

¹H-NMR (300 MHz) δ 7.89 (1H), 7.82-7.80 (2H), 7.83-7.70 (4H), 7.11-7.04(10H), 6.82 (2H), 6.65-6.59 (4H), 6.52-6.47 (7H), 1.72 (6H)

Synthesis Example 7 Synthesis of Compound 43

Compound 43 was synthesized through Reaction Scheme 8 below:

2.4 g (5.0 mmol) of Compound F and 5.01 g (15.0 mmol) ofphenyl-(phenylcarbazole) was dissolved in 200 mL of toluene. To theresultant reaction mixture was added 2.40 g (25 mmol) of t-BuONa, 137 mg(3 mol %) of Pd₂(dba)₃, and 30 mg (3 mol %) of (t-Bu)₃P, and then theresultant reaction mixture was stirred for 6 hours at 90° C.

The reaction mixture was then extracted 3 times with 100 mL ofdichloromethane and the organic layers were combined, dried overmagnesium sulfate to evaporate the solvent. The residue was subjected tosilica gel column chromatography to obtain 2.73 g (yield=56%) ofCompound 43. The structure of Compound 43 was identified using ¹H-NMR.

¹H-NMR (300 MHz) δ 7.87 (1H), 7.82 (1H), 7.76-7.72 (5H), 7.56 (2H), 7.42(2H), 7.39-7.13 (12H), 7.08-6.98 (10H), 6.81-6.46 (9H), 6.28 (2H), 1.71(6H)

Comparative Example 1

A 15 Ω/cm² (1200 Å) ITO glass substrate (available from Corning Co.) wascut to a size of 50 mm×50 mm×0.7 mm, ultrasonically washed withisopropyl alcohol for 5 minutes and then with pure water for 5 minutes,and washed again with UV ozone for 30 minutes. Then, m-MTDATA was vacuumdeposited on the substrate to form a hole injection layer having athickness of 750 Å, and then α-NPD was vacuum deposited on the holeinjection layer to form a hole transport layer having a thickness of 150Å. 97 wt % of DSA as a host and 3 wt % of TBPe as a dopant weredeposited on the HTL to form an EML with a thickness of 300 Å. Alq3 wasvacuum-deposited on the EML to form an ETL having a thickness of 200 Å.LiF was vacuum-deposited on the ETL to form an EIL having a thickness of80 Å and Al was vacuum-deposited on the EIL to form a cathode having athickness of 3000 Å.

Example 1

An OLED was manufactured in the same manner as in Comparative Example 1,except that Compound 34 was used instead of m-MTDATA to form the HTL.

Example 2

An OLED was manufactured in the same manner as in Comparative Example 1,except that Compound 40 was used instead of DSA as the host of the EML.

Example 3

An OLED was manufactured in the same manner as in Comparative Example 1,except that Compound 35 was used instead of TBPe as the dopant of theEML.

Example 4

An OLED was manufactured in the same manner as in Comparative Example 1,except that Compound 43 was used instead of Alq₃ to form the ETL.

Example 5

An OLED was manufactured in the same manner as in Comparative Example 1,except that Compound 19 was used instead of Alq₃ to form the ETL.

Example 6

An OLED was manufactured in the same manner as in Comparative Example 1,except that Compound 3 was used instead of Alq₃ to form the ETL.

Evaluation Example

Efficiency and half lifetime characteristics of the OLEDs manufacturedin Comparative Example 1 and Examples 1 through 6 were measured using aPR650 (Spectroscan) Source Measurement Unit. (available fromPhotoResearch, Inc.). The results are shown in Table 1 below.

TABLE 1 Half Lifetime Luminance (hour) @ Efficiency 1000 Compound Use ofCompound (cd/A) nit Example 1 Compound Hole Transport 4.2 3700 34 LayerExample 2 Compound Host 4.3 4200 40 Example 3 Compound Dopant 3.7 380035 Example 4 Compound Hole Transport 4.1 4200 43 Layer Example 5Compound Electron 4.4 4500 19 Transport Layer Example 6 Compound 3Electron 3.9 2600 Transport Layer Comparative — — 2.8 1400 Example

Referring to Table 1, it can be confirmed that the OLEDs of Examples 1through 6 have higher luminance efficiencies and half lifetime, comparedto the OLED of Comparative Example 1.

An OLED including an organic layer containing the condensed-cycliccompound of Formula 1 above may have high efficiency and longdurability.

While the present embodiments have been particularly shown and describedwith reference to exemplary embodiments thereof, it will be understoodby those of ordinary skill in the art that various changes in form anddetails may be made therein without departing from the spirit and scopeof the present embodiments as defined by the following claims.

What is claimed is:
 1. A condensed-cyclic compound represented byFormula 1 below:

wherein R₈ and R₇ are not identical and are each independently selectedfrom the group consisting of a hydrogen atom, a halogen atom, a hydroxylgroup, a cyano group, a substituted or unsubstituted C₁-C₃₀ alkyl group,a substituted or unsubstituted C₂-C₃₀ alkenyl group, a substituted orunsubstituted C₂-C₃₀ alkynyl group, a substituted or unsubstitutedC₁-C₃₀ alkoxy group, a group represented by —(Ar₁)_(a)—Ar₁₁, and a grouprepresented by —N[—(Ar₂)_(b)—Ar₁₂][—(Ar₃)_(c)—Ar₁₃]; or R₈ is connectedto * of Formula 2 and R₇ is connected to *′ of Formula 2 represented by:

wherein R₁ through R₆, R₁₁ through R₁₄, and R₂₁ through R₂₄ are eachindependently selected from the group consisting of a hydrogen atom, ahalogen atom, a hydroxyl group, a cyano group, a substituted orunsubstituted C₁-C₃₀ alkyl group, a substituted or unsubstituted C₂-C₃₀alkenyl group, a substituted or unsubstituted C₂-C₃₀ alkynyl group, asubstituted or unsubstituted C₁-C₃₀ alkoxy group, a group represented by—(Ar₄)_(d)—Ar₁₄, and a group represented by—N[—(Ar₅)_(c)—Ar₁₅][—(Ar₆)_(f)—Ar₁₆]; wherein Ar₁ through Ar₆ are eachindependently selected from the group consisting of a substituted orunsubstituted C₁-C₃₀ alkylene group, a substituted or unsubstitutedC₂-C₃₀ alkenylene group, a substituted or unsubstituted C₅-C₃₀ arylenegroup, and a substituted or unsubstituted C₄-C₃₀ heteroarylene group;wherein Ar₁₁ through Ar₁₆ are each independently selected from the groupconsisting of a hydrogen atom, a halogen atom, a hydroxyl group, a cyanogroup, a substituted or unsubstituted C₁-C₃₀ alkyl group, a substitutedor unsubstituted C₂-C₃₀ alkenyl group, a substituted or unsubstitutedC₂-C₃₀ alkynyl group, a substituted or unsubstituted C₁-C₃₀ alkoxygroup, a substituted or unsubstituted C₅-C₃₀ aryl group, and asubstituted or unsubstituted C₄-C₃₀ heteroaryl group; wherein a throughf are each independently an integer from 0 to 10; wherein the moietiesrepresented by Ar₁ in the group represented by —(Ar₁)_(a)—Ar₁₁ areidentical to or different from each other, the moieties represented byAr_(e) in the group represented by —(Ar₂)_(b)—Ar₁₂ are identical to ordifferent from each other, the moieties represented by Ar₃ in the grouprepresented by —(Ar₃)_(c)—Ar₁₃ are identical to or different from eachother, the moieties represented by Ar₄ in the group represented by—(Ar₄)_(d)—Ar₁₄ are identical to or different from each other, themoieties represented by Ar₅ in the group represented by —(Ar₅)_(e)—Ar₁₅are identical to or different from each other, and the moietiesrepresented by Ar₆ in the group represented by [—(Ar₆)_(f)—Ar₁₆] areidentical to or different from each other; wherein X₁ and X₂ are eachindependently a divalent linking group selected from the groupconsisting of —C(Q₁)(Q₂)- and —N(Q₃)-; and wherein Q₁ through Q₃ areeach independently selected from the group consisting of a hydrogenatom, a halogen atom, a hydroxyl group, a cyano group, a substituted orunsubstituted C₁-C₃₀ alkyl group, a substituted or unsubstituted C₂-C₃₀alkenyl group, a substituted or unsubstituted C₂-C₃₀ alkynyl group, asubstituted or unsubstituted C₁-C₃₀ alkoxy group, a substituted orunsubstituted C₅-C₃₀ aryl group, and a substituted or unsubstitutedC₄-C₃₀ heteroaryl group.
 2. The condensed-cyclic compound of claim 1,wherein R₁, R₂ R₃ R₄, R₅, R₆, and R₇ are hydrogen; R₈ is selected fromthe group consisting of a substituted or unsubstituted C₁-C₁₀ alkylgroup, a substituted or unsubstituted C₂-C₁₀ alkenyl group, asubstituted or unsubstituted C₂-C₁₀ alkynyl group, a substituted orunsubstituted C₁-C₁₀ alkoxy group, a group represented by—(Ar₁)_(a)—Ar₁₁, and a group represented by—N[—(Ar₂)_(b)—Ar₁₂][—(Ar₃)_(c)—Ar₁₃]; R₁₁, R₁₂, R₁₃ and R₁₄ are eachindependently selected from the group consisting of hydrogen, asubstituted or unsubstituted C₁-C₁₀ alkyl group, a substituted orunsubstituted C₂-C₁₀ alkenyl group, a substituted or unsubstitutedC₂-C₁₀ alkynyl group, a substituted or unsubstituted C₁-C₁₀ alkoxygroup, a group represented by —(Ar₄)_(d)—Ar₁₄, and a group representedby —N[—(Ar₅)_(e)—Ar₁₅][—(Ar₆)_(f)—Ar₁₆]; Ar₁, Ar₂, Ar₃, Ar₄, Ar₅ and Ar₆are each independently selected from the group consisting of asubstituted or unsubstituted C₁-C₃₀ alkylene group, a substituted orunsubstituted C₂-C₃₀ alkenylene group, a substituted or unsubstitutedC₅-C₃₀ arylene group, and a substituted or unsubstituted C₄-C₃₀heteroarylene group; and Ar₁₁ and Ar₁₆ are each independently selectedfrom the group consisting of a hydrogen atom, a halogen atom, a hydroxylgroup, a cyano group, a substituted or unsubstituted C₁-C₃₀ alkyl group,a substituted or unsubstituted C₂-C₃₀ alkenyl group, a substituted orunsubstituted C₂-C₃₀ alkynyl group, a substituted or unsubstitutedC₁-C₃₀ alkoxy group, a substituted or unsubstituted C₅-C₃₀ aryl group,and a substituted or unsubstituted C₄-C₃₀ heteroaryl group.
 3. Thecondensed-cyclic compound of claim 2, wherein a, b, c, d, e and f areeach independently 0, 1, or
 2. 4. The condensed-cyclic compound of claim2, wherein Ar₁, Ar₂, Ar₃, Ar₄, Ar₅ and Ar₆ are each independentlyselected from the group consisting of a pyridinylene group, aquinolinylene group, a benzimidazolylene group, an imidazopyridinylenegroup, an imidazopyrimidinylene group, a phenylene group, a C₁-C₁₀ alkylphenylene group, a carbazolylene group, a phenylcarbazolylene group, afluorenylene group, a C₁-C₁₀ alkylfluorenylene group, adi(C₁-C₁₀alkyl)fluorenylene group, an ethylene group, and a naphthylenegroup.
 5. The condensed-cyclic compound of claim 2, wherein Ar₁₁ Ar₁₂,Ar₁₃, Ar₁₄, Ar₁₅ and Ar₁₆ are each independently selected from the groupconsisting of a methyl group, ethyl, a propyl group, a butyl group, amethoxy group, an ethoxy group, a propoxy group, a butoxy group, apyridinyl group, a quinolinyl group, a benzimidazolyl group, animidazopyridinyl group, an imidazopyrimidinyl group, a phenyl group, acarbazolyl group, a fluorenyl group, a di(C₁-C₁₀alkyl)fluorenyl group, anaphthyl group, and a functional group prepresented by the formula


6. The condensed-cyclic compound of claim 2, wherein R₈ is selected fromthe group consisting of functional groups represented by Formulae 3Athrough 3O below

and R₁₁, R₁₂, R₁₃ and R₁₄ are each independently selected from the groupconsisting of hydrogen and functional groups represented by Formulae 3Athrough 3O below:

wherein, in Formulae 3A through 3O, Z₁ and Z₂ are each independentlyselected from the group consisting of hydrogen, a methyl group, an ethylgroup, a propyl group, a butyl group, a methoxy group, an ethoxy group,a propoxy group, a butoxy group, a phenyl group, and a naphthyl group.7. The condensed-cyclic compound of claim 2, wherein R8 is selected fromthe group consisting of functional groups represented by Formula 4Athrough 4R below

and R₁₁ R₁₂, R₁₃ and R₁₄ are each independently selected from the groupconsisting of hydrogen and functional groups represented by Formulae 4Athrough 4R below:


8. The condensed-cyclic compound of claim 2, wherein Q₁ through Q₃ areeach independently selected from the group consisting of hydrogen, aC₁-C₃₀ alkyl group, a C₁-C₃₀ alkoxy group, a C₅-C₁₄ aryl group, and aC₄-C₁₄ heteroaryl group.
 9. The condensed-cyclic compound of claim 1,wherein R₈ is connected to * of Formula 2 and R₇ is connected to *′ ofFormula 2 so as to be represented by Formula 1a below:


10. The condensed-cyclic compound of claim 9, wherein R₁ R₂, R₃, R₄, R₅and R₆ are hydrogen; R₁₁ R₁₂, R₁₃, R₁₄ R₂₁ R₂₂, R₂₃ and R₂₄ are eachindependently selected from the group consisting of hydrogen, asubstituted or unsubstituted C₁-C₁₀ alkyl group, a substituted orunsubstituted C₂-C₁₀ alkenyl group, a substituted or unsubstitutedC₂-C₁₀ alkynyl group, a substituted or unsubstituted C₁-C₁₀ alkoxygroup, a group represented by —(Ar₄)_(d)—Ar₁₄, and a group representedby —N[—(Ar₅)_(e)—Ar₁₅][—(Ar₆)_(f)—Ar₁₆]; Ar₄, Ar₅ and Ar₆ are eachindependently selected from the group consisting of a substituted orunsubstituted C₁-C₃₀ alkylene group, a substituted or unsubstitutedC₂-C₃₀ alkenylene group, a substituted or unsubstituted C₅-C₃₀ arylenegroup, and a substituted or unsubstituted C₄-C₃₀ heteroarylene group;and Ar₁₄ and Ar₁₆ are each independently selected from the groupconsisting of a hydrogen atom, a halogen atom, a hydroxyl group, a cyanogroup, a substituted or unsubstituted C₁-C₃₀ alkyl group, a substitutedor unsubstituted C₂-C₃₀ alkenyl group, a substituted or unsubstitutedC₂-C₃₀ alkynyl group, a substituted or unsubstituted C₁-C₃₀ alkoxygroup, a substituted or unsubstituted C₅-C₃₀ aryl group, and asubstituted or unsubstituted C₄-C₃₀ heteroaryl group.
 11. Thecondensed-cyclic compound of claim 9, wherein d, e and f are eachindependently 0, 1, or
 2. 12. The condensed-cyclic compound of claim 9,Ar₄, Ar₅ and Ar₆ are each independently selected from the groupconsisting of a pyridinylene group, a quinolinylene group, abenzimidazolylene group, an imidazopyridinylene group, animidazopyrimidinylene group, a phenylene group, a C₁-C₁₀ alkyl phenylenegroup, a carbazolylene group, a phenylcarbazolylene group, afluorenylene group, a C₁-C₁₀ alkyl fluorenylene group, a di(C₁-C₁₀alkyl) fluorenylene group, an ethylene group, and a naphthylene group.13. The condensed-cyclic compound of claim 9, wherein Ar₁₄, Ar₁₅ andAr₁₆ are each independently selected from the group consisting of amethyl group, an ethyl group, a propyl group, a butyl group, a methoxygroup, an ethoxy group, a propoxy group, a butoxy group, a pyridinylgroup, a quinolinyl group, a benzimidazolyl group, an imidazopyridinylgroup, an imidazopyrimidinyl group, a phenyl group, a carbazolyl group,a fluorenyl group, di(C₁-C₁₀ alkyl)fluorenyl group, a naphthyl group,and a functional group prepresented by the formula


14. The condensed-cyclic compound of claim 9, wherein R₁₁ R₁₂, R₁₃, R₁₄R₂₁ R₂₂, R₂₃ and R₂₄ are each independently selected from the groupconsisting of hydrogen and functional groups represented by Formulae 3Athrough 3O below:

wherein, in Formulae 3A through 3O, Z₁ and Z₂ are each independentlyselected from the group consisting of hydrogen, a methyl group, an ethylgroup, a propyl group, a butyl group, a methoxy group, an ethoxy group,a propoxy group, a butoxy group, a phenyl group, and a naphthyl group.15. The condensed-cyclic compound of claim 9, wherein R₁₁ R₁₂, R₁₃ R₁₄R₂₁ R₂₂, R₂₃ and R₂₄ are each independently selected from the groupconsisting of hydrogen and functional groups represented by Formulae 4Athrough 4R below:


16. The condensed-cyclic compound of claim 9, wherein Q₁, Q₂ and Q₃ areeach independently selected from the group consisting of hydrogen, aC₁-C₃₀ alkyl group, a C₁-C₃₀ alkoxy group, a C₅-C₁₄ aryl group, and aC₄-C₁₄ heteroaryl group.
 17. A condensed-cyclic compound having thestructure of compounds 1 to 6 and 13 to 43 below:


18. An organic light emitting diode comprising: a first electrode; asecond electrode facing the first electrode; and an organic layerdisposed between the first electrode and the second electrode; whereinthe organic layer comprises the condensed-cyclic compound of claim 1.19. The organic light emitting diode of claim 18, wherein the organiclayer is a hole transport layer, an emissive layer, or an electrontransport layer.
 20. The organic light emitting diode of claim 18,further comprising, between the first electrode and the secondelectrode, at least one layer selected from the group consisting of ahole injection layer, a hole transport layer, an emissive layer, a holeblocking layer, an electron transport layer, and an electron injectionlayer.
 21. A condensed-cyclic compound represented by Formula 1 below:

wherein R₇ is selected from the group consisting of a hydrogen atom, ahalogen atom, a hydroxyl group, a cyano group, a substituted orunsubstituted C₁-C₃₀ alkyl group, a substituted or unsubstituted C₂-C₃₀alkenyl group, a substituted or unsubstituted C₂-C₃₀ alkynyl group, asubstituted or unsubstituted C1-C30 alkoxy group, a group represented by—(Ar₁)_(a)—Ar₁₁, and a group represented by—N[—(Ar₂)_(b)—Ar₁₂][—(Ar₃)_(c)—Ar₁₃] and R₈ is selected from the groupconsisting of a halogen atom, a hydroxyl group, a cyano group, asubstituted or unsubstituted C₁-C₃₀ alkyl group, a substituted orunsubstituted C₂-C₃₀ alkenyl group, a substituted or unsubstitutedC₂-C₃₀ alkynyl group, a substituted or unsubstituted C₁-C₃₀ alkoxygroup, a group represented by —(Ar₁)_(a)—Ar₁₁, and a group representedby —N[—(Ar₂)_(b)— Ar₁₂][—(Ar₃)_(c)—Ar₁₃]; or R₈ is connected to * ofFormula 2 and R₇ is connected to *′ of Formula 2 represented by:

wherein R₁ through R₆, R₁₁ through R₁₄, and R₂₁ through R₂₄ are eachindependently selected from the group consisting of a hydrogen atom, ahalogen atom, a hydroxyl group, a cyano group, a substituted orunsubstituted C₁-C₃₀ alkyl group, a substituted or unsubstituted C₂-C₃₀alkenyl group, a substituted or unsubstituted C₂-C₃₀ alkynyl group, asubstituted or unsubstituted C₁-C₃₀ alkoxy group, a group represented by—(Ar₄)_(d)—Ar₁₄, and a group represented by—N[—(Ar₅)_(e)—Ar₁₅][—(Ar₆)_(f)—Ar₁₆]; wherein Ar₁ through Ar₆ are eachindependently selected from the group consisting of a substituted orunsubstituted C₁-C₃₀ alkylene group, a substituted or unsubstitutedC₂-C₃₀ alkenylene group, a substituted or unsubstituted C₅-C₃₀ arylenegroup, and a substituted or unsubstituted C₄-C₃₀ heteroarylene group;wherein Ar₁₁ is selected from the group consisting of a halogen atom, ahydroxyl group, a cyano group, a substituted or unsubstituted C₁-C₃₀alkyl group, a substituted or unsubstituted C₂-C₃₀ alkenyl group, asubstituted or unsubstituted C₂-C₃₀ alkynyl group, a substituted orunsubstituted C₁-C₃₀ alkoxy group, a substituted or unsubstituted C₅-C₃₀aryl group, and a substituted or unsubstituted C₄-C₃₀ heteroaryl group;wherein Ar₁₂ through Ar₁₆ are each independently selected from the groupconsisting of a hydrogen atom, a halogen atom, a hydroxyl group, a cyanogroup, a substituted or unsubstituted C₁-C₃₀ alkyl group, a substitutedor unsubstituted C₂-C₃₀ alkenyl group, a substituted or unsubstitutedC₂-C₃₀ alkynyl group, a substituted or unsubstituted C₁-C₃₀ alkoxygroup, a substituted or unsubstituted C₅-C₃₀ aryl group, and asubstituted or unsubstituted C₄-C₃₀ heteroaryl group; wherein a throughf are each independently an integer from 0 to 10; wherein the moietiesrepresented by Ar₁ in the group represented by —(Ar₁)_(a)—Ar₁₁ areidentical to or different from each other, the moieties represented byAr₂ in the group represented by —(Ar₂)_(b)—Ar₁₂ are identical to ordifferent from each other, the moieties represented by Ar₃ in the grouprepresented by —(Ar₃)_(c)—Ar₁₃ are identical to or different from eachother, the moieties represented by Ar₄ in the group represented by—(Ar₄)_(d)—Ar₁₄ are identical to or different from each other, themoieties represented by Ar₅ in the group represented by —(Ar₅)_(e)—Ar₁₅are identical to or different from each other, and the moietiesrepresented by Ar₆ in the group represented by [—(Ar₆)_(f)—Ar₁₆] areidentical to or different from each other; wherein X₁ and X₂ are eachindependently a divalent linking group selected from the groupconsisting of —C(Q₁)(Q₂)- and —N(Q₃)-; and wherein Q₁ through Q₃ areeach independently selected from the group consisting of a hydrogenatom, a halogen atom, a hydroxyl group, a cyano group, a substituted orunsubstituted C₁-C₃₀ alkyl group, a substituted or unsubstituted C₂-C₃₀alkenyl group, a substituted or unsubstituted C₂-C₃₀ alkynyl group, asubstituted or unsubstituted C₁-C₃₀ alkoxy group, a substituted orunsubstituted C₅-C₃₀ aryl group, and a substituted or unsubstitutedheteroaryl group.